Reaction #465944

Reaction equation

4-[N,N-bis(3,4-dimethylphenyl)amino]benzaldehyde

trimethylphosphonium bromide

sodium hydride

→

4-[N,N-bis(3,4-dimethylphenyl)amino]styrene

Yield 85.0%

Solvents

1,2-dimethoxyethane

Conditions

Workup

1. 1
   Otherreaction at 700° C. for 5 hours
2. 2
   Filtrationfollowed by filtration
3. 3
   Otherto collect a cake
4. 4
   ExtractionThe cake was extracted with ether
5. 5
   Washwashed with water
6. 6
   Otherthe ether was removed
7. 7
   Otherto obtain a crude product
8. 8
   OtherAfter twice recrystallized from ethanol

Procedure

Into a three-necked flask, 12.1 g of sodium hydride and 580 ml of 1,2-dimethoxyethane were placed, and 108.5 g of trimethylphosphonium bromide was added thereto with stirring at room temperature. Next, after a drop of absolute alcohol was added, the reaction was allowed to proceed at 70° C. for 4 hours. Then, 100.0 g of 4-[N,N-bis(3,4-dimethylphenyl)amino]benzaldehyde was added to the reaction mixture, to carry out reaction at 700° C. for 5 hours, followed by filtration to collect a cake. The cake was extracted with ether and the extract was put together with the filtrate and washed with water. Then, the ether solution was dehydrated with calcium chloride, and thereafter the ether was removed to obtain a crude product. After twice recrystallized from ethanol, acicular 4-[N,N-bis(3,4-dimethylphenyl)amino]styrene was obtained in an amount of 84.5 g (yield: 85.0%).

Source